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Cheap Flights from Chicago to Oakland $246.0

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Cheapest Flights from Chicago to Oakland (MDW to OAK)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from Chicago to Oakland (MDW to OAK)

Question : Can you cut down on flight costs by changing the day of the week you travel to Oakland?
Answer : For the month of December, the cheapest day to fly is Monday. Having flexibility in your travel plans means you can save, so be sure to plan ahead when possible.

Question : How many departure times from Chicago Midway International Airport (MDW) to Metropolitan Oakland International Airport (OAK) are there on a daily basis?
Answer : On average, there are nine options. Compared to the average route with 31 flight times, you won't have as many options as other routes.

Question : If punctuality is required for you to book a flight, which airline is your best bet?
Answer : Southwest Airlines will have you to OAK on schedule 81% of the time. Spend as little time in an airport as necessary by flying with Southwest Airlines. If they are late for some reason though, the average delay time is 10-20 minutes.

Question : Looking for the quickest flight from MDW to OAK?
Answer : Southwest Airlines currently has the quickest travel time with 30 minutes. For example, you would arrive in Oakland at 10:15 AM PST if you left Chicago at 7:45 AM. Remember, there is a two-hour time difference.

Question : Which airline is least likely to get you to OAK on time?
Answer : If you decide to book your flight with Delta Air Lines, keep an eye on your departure time. Delta Air Lines flights from Chicago Midway International Airport (MDW) to Metropolitan Oakland International Airport (OAK) are late 50% of the time.

Question : Which day has the most flight time options?
Answer : With 49 total flight time options, Wednesday provides the most flexibility from MDW to OAK. The day with the least number of options is Saturday with 31 different times.